HCID 15407200, compound → HCID 517029, compound

HRID 1368871Notes

Reaction equation

HRID 1368871 reaction equation
CC(C)C(P(=O)O)NC(=O)CCC1C=CC=CC=1.C(OC([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][C@H:34]([OH:45])[C:35]([O:37]CC1C=CC=CC=1)=[O:36])=O)C1C=CC=CC=1>ClCCl>[NH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH:34]([OH:45])[C:35]([OH:37])=[O:36]

Participants

4

Reactant 2

HCID 15407200HCID 15407200, compoundHCID 178449450HCID 178449450, compound

Product 1

HCID 517029HCID 517029, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, a dichloromethane (15 ml) solution of the 2-methyl-1-(3-phenylpropanoylamino)propylphosphinic acid (162 mg) obtained in the above step (a) was added with benzyl (S)-6-benzyloxycarbonylamino-2-hydroxyhexanoate (228 mg) which was obtained from 6-amino-2-hydroxyhexanoic acid described in Chem. Pharm. Bull., 621(1976) in a conventional manner, N-(dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (180 mg), and dimethylaminopyridine (38.7 mg), and then the mixture was stirred at room temperature for 16 hours. The organic substances were extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (10 g, chloroform:methanol=10:1) to obtain benzyl (S)-6-(benzyloxycarbonylamino)-2-((2-methyl-1-(3-phenylpropanoylamino)propyl)phosphinoyloxy)hexanoate (117 mg, 31%). This compound was subjected to the measurement of molecular weight and then used in the following reaction.

Sources & evidence

ORD record
ord-469341d5de4e4515ac179ab74eda2a85
Source dataset
uspto-grants-2003_06
Patent number
US06576627B1

Reaction notes

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